My instructions for importing audiobooks from different CD formats into iTunes have inspired a lot of follow-up questions. To help keep things organized, I’ve moved them and my answers from the comments where they originated to this FAQ.

I love questions, so please feel free to send them to me at the email address in the sidebar. I generally respond in a couple days, and try to publish them here as well as reply via email. More questions means more answers, and a better experience for everyone.

How do I get my audiobook to appear in the Audiobooks menu on my iPod or iPhone?

Select the tracks you want iTunes and your devices to treat as audiobooks.

Choose File > Get Info.

In the item information dialog, select the Options tab.

Set the Media Kind to Audiobook.

Click OK.

Now sync with your device to copy the updated tracks to it. They should now appear in the Audiobooks menu.

How do I get my audiobook to appear in the LIBRARY > Books source list in iTunes?

See the previous answer. All tracks with a Media Kind of Book or Audiobook will appear in the Books source list in iTunes.

Is there a way to sort or group the audiobook tracks in the Audiobooks menu on my iPod? Like, say, by author, or by book, instead of listing every single individual book track?

The short answer is, unfortunately, no. The Audiobooks menu is listed strictly by track name, which means you can end up with quite a few items listed which look identical, because they are for the same book, with the only difference being a “xx of yy” at the end of the track name.

However, you can access your audiobooks via the Genres > Audiobooks menu instead. There you will find your books grouped by author, and under author grouped by book title. It’s a few too many scroll-and-clicks for my taste, but it beats trying to find the seventh track of a book with a long title by counting down the list in Audiobooks because the long title pushes the track numbers off-screen on your iPod mini. Which happens to me quite often…

When I play back the discs on my iPod, they are playing in a random order. How do I make the book play in the right order?

Here are three things to try:

Make sure that Shuffle Mode is turned off: Settings > Shuffle > Off.

Make sure you’ve named the tracks in such a way that sorting them in name order is the right order, e.g., “Kill the Messenger 01”, “Kill the Messenger 02”, etc.

Make sure you’ve put the right track number and disc number information onto all the tracks. I leave the track numbers blank, and use the disc number only. It should be numbered sequentially, just like in the file names, except you don’t need leading zeros. This is frequently the problem; the straight importing procedure can leave semi-random information in the track fields if you are not careful to clear it out.

As a last resort, you can create a new Playlist in iTunes, and manually add and order all of the tracks for the book. Then you will need to access the book via the Music > Playlists menu, but the tracks should appear in the right order.

Isn’t the AAC format a proprietary Apple audio format? Isn’t it less compatible with audioplayers?

The instructions I provide on this site import audiobooks into AAC format, an industry standard format. You can get more information from Apple’s AAC page or Wikipedia’s more detailed entry. There are a number of ways in which it is better than the MP3 format, but because it is a newer standard, it may be unsupported on older devices. But as an open standard, anyone can support it, and many do. Details at those links.

An important distiction to make is in regards to the Protected AAC format, which is an AAC format track wrapped in Apple’s FairPlay DRM system. These tracks are indeed not compatible with players besides the iPod and iTunes, and other Apple devices. But this is because of the DRM, not because of AAC.

Why is the Join CD Tracks menu item dimmed in the Advanced menu?

There are two reasons why this command might be dimmed. The first is that you’ve got something besides CD tracks selected, i.e., even one track which is already in your library. For whatever reason, iTunes can only join tracks before they are imported from a CD, so anything besides what’s on the CD will cause the menu command to be dimmed.

The second reason why this menu item might be dimmed is much more subtle. The track list of the CD must be sorted by the track number column (which isn’t labeled). If it’s sorted by any other column, the menu command will be dimmed. The track number column is the left-most column of the songs list, as displayed here:

Is it possible to join the tracks of already existing albums or is that done as part of the recording process?

Will these instructions work with an iPod shuffle?

I don’t think the iPod shuffle is well-suited to audiobook playback. It is not impossible, but it is certainly painful (Rochelle tried it for a couple weeks after her old iPod died on a trip). If you are not dissuaded, read more details in the article Which iPod Should I Buy?.

I use iTunes, but I don’t have an iPod, I have a different player. Will these instructions work for me?

If you change your import settings to use the MP3 format instead of the AAC format, you can probably get the files to work on almost any brand of digital audio player, even older ones. But since iTunes only synchronizes (gracefully) with iPods, you’ll have to figure out how to transfer the files to your player on your own.

But I can say, from personal experience with another digital audio player, that other players do not work nearly as well as an iPod. I would recommend that every serious audiobook aficionado get an iPod! They are not substantially more expensive, and they are worth it. The iPod is much better designed, and you get to use it seamlessly with iTunes. The one-two combination of iTunes and iPod blows everything else out of the water; that’s the reason I started writing these instructions.

Many public libraries now allow you to “check out” downloadable versions of audio books, just like checking out tape or CD versions, but more convenient. But they won’t play on an iPod! Is there a way to get them to play on an iPod?

The short answer is no, there is no way to get these versions to play on an iPod. The audiobooks are wrapped in a Microsoft Windows-only digital rights management (DRM) encoding, to prevent the books from being copied. Breaking the DRM to play the books on an iPod is illegal under current US law (as well as in many other countries). (Under US law, it’s even illegal to point at someone else’s instructions for breaking the Windows DRM. So, you’re not going to find that information here.)

Libraries want to be as accessible as possible to their patrons. That’s why they are experimenting with the current downloadable options. But IMHO the current solutions do not serve patrons very well (and I bet the libraries trying them out would say as much). It seems to me that it’s a poor use of taxpayer money to license digital versions of audiobooks which cannot be played on the handheld audio player with 80% of the market, and which surely pose technical challenges even for the patrons with devices that can play them.

I believe it is in everyone’s interest for libraries to instead acquire audiobooks in standard Audio CD format. These will be compatible with all players on all devices, including players that don’t involve a computer (which are a challenge for many patrons).

For iPod owners the best best is to pester engage in a dialog with our libraries about compatibility with the iPod, and request that they spend their audiobook budget on additional books on CD, which a wider range of library users can enjoy.

The CDs I’m trying to import are scratched, and iTunes can’t read them, or the audio skips or gets corrupted. Is there anything I can do?

This will cause iTunes to do additional work when importing your CDs, to try to mitigate the effects of the physical damage. It takes longer, sometimes a lot longer, but it can result in successful imports in cases where the CD is partially unreadable.

The second possibility involves using a third-party tool that has the cdparanoia feature. On Mac OS X, you can use the Max application, which is free and Open Source. On Windows you can use either Exact Audio Copy (EAC) or CDex. I’ve not tested either, yet, but EAC looks like it’s a little easier to use.

I have all my audiobooks on cassette tapes. Is there any way to get them onto my iPod?

It’s not impossible, but unfortunately there is no way I know of to directly import an audiocassette into iTunes. The reason CDs are relatively easy to import into iTunes, and then transfer onto an iPod, is because you can insert CDs into your computer and read the data off of them. It’s virtually impossible to buy a computer without a CD drive of some sort. But the same is not true of cassettes.

A couple of readers have pointed me at a tape player designed to be installed into a PC, called the Plus Deck ($150 at ThinkGeek). It looks like a pretty cool product, and while it doesn’t integrate directly with iTunes, you could probably use the included software to digitize tapes, and then drag the resulting files into iTunes easily enough. If you already have a sizable collection of audiobooks on tape, this could be a terrific solution. (If you try it out, please let me know what you think!)

If buying new, single-purpose hardware isn’t possible, or you’re on a Mac, some computers come with line in or microphone ports, to which you could connect a tape player, and then use the combo to re-record your tapes into digital form on the computer, but that takes additional software (Audacity is both free and well-regarded) and considerably more effort. At least for now, that’s not something I’m going to try, so I can’t document it, but these two guides may be useful. Update: Mac users, here’s a newer article that covers how to digitize both your cassettes and LPs.

There are certainly articles online that talk about converting cassette tapes to MP3s, which you could use as instructions (if you find a good set, let me know the URL, and I’ll post it here). Once you have MP3s of your cassettes, it’s a trivial exercise to add them to iTunes. Then you can add the audiobook meta information (title, author, etc.), and you’re off to the races.

My computer crashed, and I lost all of my audiobooks (or music, or whatever). Is there any way to copy them from my iPod back to my computer?

The folks at iLounge have covered this much better than I can, so I will simply point to their article: